Tom Dreesen, the classy comedian who opened for Frank Sinatra for 14 years, pushed for stand-ups to get paid at The Comedy Store and partnered in a pioneering interracial act with Tim Reid, died Wednesday. He was 86.

Dreesen died at his home in Los Angeles, a family spokesperson told The Hollywood Reporter. No cause of death was revealed.

The pride of Chicago, Dreesen made hundreds of TV appearances during his 50-plus years in show business, including dozens on The Tonight Show Starring Johnny Carson and on the late-night programs hosted by David Letterman, his dear friend from their days in the 1970s at The Comedy Store in West Hollywood.

Always thought-provoking but never controversial, few were better at delivering a joke.

“I don’t know if you know this or not, but in 1871 in baseball, men started wearing the cup to protect the family jewels,” Dreesen quipped during a gig at the Laugh Factory. “In 1971, it became mandatory to wear a helmet. It took men 100 years to realize the brain is important also.”

After warming up audiences for the likes of Liza Minnelli, Smokey Robinson, Gladys Knight and Sammy Davis Jr., the always dapper Dreesen began sharing a bill with Sinatra in 1983 and shared a special camaraderie with the Chairman of the Board during the singer’s twilight years.

As Dreesen explained it during a 2014 interview with The Desert Sun, it was a mixture of serendipity and quick wit that landed him his highest-profile gig.

The comic had opened for Robinson in Lake Tahoe and was running through the lobby to see Sinatra headlining next door when he was stopped by Holmes Hendrickson, a vice president of Harrah’s, and introduced to Mickey Rudin.

“I recognized the name as Frank’s lawyer, and [Hendrickson] said, ‘Tom would make a great opening act for Sinatra,'” Dreesen recalled. “[Rudin] said, ‘Hey, kid, if I gave you a week with Frank, would you want more than $50,000?’ I said, ‘Mr. Rudin, put it this way. If you gave me a week with Frank, would you want more than $50,000?’ He said, ‘I like this kid.'”

Dreesen soon was opening for Sinatra in Atlantic City, and he never imagined the impact it would have on his life. “I thought, ‘Yeah, I’ll go one week. I’ll get my picture taken and I’ll hang it in every bar back in Chicago and that will be the end of that,'” he said.

“On the second night, Frank and his wife, Barbara, took me to dinner, and in the middle of dinner he put down his knife and his fork. He said, ‘Kid, I like your material. I like your style. I’d like you to do a few other dates with me if you’re interested.’ I said, ‘Yeah!’ and it turned into 14 years, 45 to 50 cities a year.”

The two developed a deep friendship, and Dreesen often visited Sinatra at his compound in Palm Springs. He served as a pall bearer and spoke at the entertainer’s funeral in 1998 and for years hosted the Frank Sinatra Celebrity Invitational Black Tie Gala.

“If he loved you, he worshiped the ground you walked on,” Dreesen said. “In a lot of ways, he was like a father to me. I didn’t have a father that really cared that much where I was and what I did. But Frank would give me advice and counsel and then he was a buddy in a lot of ways. I thought the world of him.”

Before he met Sinatra, Dreesen led a charge that changed the course of comedy.

For years, stand-up was centered in New York and Las Vegas, but that all changed in 1972 when Carson brought The Tonight Show from Manhattan to Los Angeles. Suddenly, The Comedy Store on Sunset Boulevard became the place to be seen.

Run by Mitzi Shore, who was given the club as part of a divorce settlement with her husband, Sammy Shore, The Comedy Store became a kind of college for comedians. And because she was giving them such a valuable opportunity, she believed there was no need to pay them. Dreesen, in the process of establishing his career, disagreed.

“I told Mitzi, ‘You pay the waiters, you pay the waitresses, you pay the guy who cleans the toilets. Why don’t you at least pay the comedians?'” Dreesen told Richard Zoglin in an interview for the 2008 book Comedy at the Edge: How Stand-Up in the 1970s Changed America.

He spoke with Shore about one comic who had been on her stage on New Year’s Eve. “He said, ‘It was fantastic. I killed ’em,'” Dreesen said. “And then he said, ‘Tom, can you loan me $5 for breakfast?’ I told Mitzi that story, and she said, ‘Well, he should get a goddamn job.’ I said, ‘Mitzi, he has a job. He worked for you on New Year’s Eve.'”

When Shore refused to cut the comedians in on her profits, Dreesen, drawing upon his days as a Chicago teamster, organized a strike in 1979. Letterman, Garry Shandling and Jay Leno were among those parading in front of the club waving placards that read, “NO MONEY, NO FUNNY” and “THE YUK STOPS HERE.”

After six contentious weeks and a tension-filled confrontation that saw an anti-strike comic drive his car into the picket line, Shore caved. “Mitzi called me 10 minutes later and said, ‘Let’s settle this thing right now,'” said Dreesen.

The Comedy Store started paying performers, New York clubs followed suit, and places around the country began offering more to comics. Dreesen’s leadership was instrumental in transforming the business of stand-up.

Dreesen was born on Sept. 11, 1939, in Harvey, Illinois. His father, Walter, was a trumpet player who met his future wife, Glenore, when he joined a band led by her brother-in-law, Frank Polizzi. Polizzi also owned a neighborhood bar, and Dreesen’s mom worked there as a bartender.

One of eight children, Dreesen grew up poor. His dad worked factory jobs to make ends meet but drank and gambled away most of his paycheck. Eventually, however, Dreesen learned that the man he thought was his uncle was actually his biological father.

As Rick Kogan of the Chicago Tribune wrote in 2019, “Dreesen was 12 when he said to Polizzi, ‘I think you’re my father. I look like you. I look like your son. And I don’t look like anybody in my family.’ There was quiet and then Polizzi said, ‘I am your father. But I need you to know I had affection for your mom and your mom had affection for me. I’m saying this because I don’t want you to think that we were some one-night stand.'”

When he was 17 and attending Thornton Township High School, Dreesen enlisted in the U.S. Navy and got three meals a day for the first time in his life. After the service, he meandered through jobs in construction and bartending and earned his union card on a Chicago loading dock.

While he was selling insurance, one of his brothers urged him to join the civic group known as the Jaycees. “That was when life began to change,” he said. “I was hanging around in bars where everybody moans and complains but does nothing about it. The Jaycees were gentlemen of action.”

The group recruited Dreesen and Reid, a Black marketing representative who had recently moved to Chicago from Virginia, to speak about a drug-education program geared toward grammar-school students. The pair realized that the funnier they were, the more responsive the kids were to their message. And then they formed a comedy act.

Tim & Tom made their debut in 1969 at a jazz club in South Chicago, and as the first interracial comedy team, they skewered racial stereotypes. One of their routines, “47th and Drexel,” had Reid teaching Dreesen about “being Black.”

“Hey, you got to pass a test before I turn you loose on some South Side of some city,” Reid tells Dreesen, instructing him to talk like a brother. “A looka here, Leroy,” Dreesen responds in an exaggerated jive voice. “Do the bus stop here?”

“What do you think this is, Amos ‘n’ Andy?” answers Reid. “Do the bus stop here?! You’re going to die of natural causes — some dude in a natural is going to kill you.”

Tim & Tom worked Playboy clubs, opened for George Clinton and Sha Na Na and appeared in 1971 on The David Frost Show. But they would encounter resistance.

“The fourth time we were onstage, a guy put a lit cigarette out on Tim’s face. Another guy beat the hell out of me. A year later, at the University of Illinois, I got hit in the face by an ice bar outside in the snow,” Dreesen said.

“If we worked a Black club where there was a Black guy who hated white people with a passion, he wasn’t mad at me. He was mad at Tim because he would be an Uncle Tom. We worked a white club where a redneck hated Black people, and he wasn’t mad at Tim, he was mad at me. In time, the frustration was too much. There are some people who profit by keeping the races apart. They ended up breaking up the act. They didn’t break up the friendship.”

After the split, Dreesen did solo stand-up and Reid found stardom as the velvety-voiced radio DJ Venus Flytrap on the CBS sitcom WKRP in Cincinnati (Dreesen would guest star on a 1982 episode). The duo’s story was told in Ron Rapoport’s 2008 book, Tim & Tom: An American Comedy in Black and White.

Meanwhile, Dreesen got laughs on everything from American Bandstand and Soul Train to The Jim Nabors Show and The Dean Martin Celebrity Roast; was a fixture on such game shows as Hollywood Squares, Match Game and The $10,000 Pyramid; played himself in the 1998 HBO movie The Rat Pack; and appeared on the big screen in They Call Me Bruce? (1982), Spaceballs (1987) and Man on the Moon (1999).

His autobiography, Still Standing: My Journey From Streets and Saloons to the Stage, and Sinatra — complete with a foreword from Letterman, who wrote that Dreesen “has entertained every president from Trump to Oprah” — was published in 2020.

Survivors include his children, Amy, Tom and Jennifer, from his 1958-84 marriage to Maryellen Subock.